1. Field of the Invention
The present invention relates to a method for producing (1R)-trans-2,2-dimethyl-3-(substituted vinyl)cyclopropane-1-carboxylic acid.
2. Description of the Related Art
2,2-dimethyl-3-(substituted vinyl)cyclopropane-1-carboxylic acids, which are represented by the general formula (1): ##STR2##
(wherein X is a hydrogen atom or a chlorine atom; and Y is a methyl group when X is a hydrogen atom, whereas Y is a methyl group or a fluorine atom when X is a chlorine atom) constitute the acid components of esters collectively called a synthetic pyrethroid having a highly effective insecticidal activity.
Since these cyclopropanecarboxylic acids have asymmetric carbon atoms in C.sup.1 and C.sup.3 positions thereof, there are 4 stereoisomers of cyclopropanecarboxylic acid. And, the pesticidal activity of the pyrethroid, whose acid component is one of these stereoisomers, varies according to target noxious insects, kinds of formulation, and the like. Accordingly, there is a demand for a method by which a desired specific stereoisomer of the cyclopropanecarboxylic acid is produced in an industrially advantageous way.
Under these circumstance, after intense studies for the establishment of an industrially advantageous method for producing (1R)-trans-2,2-dimethyl-3-(substituted vinyl)cyclopropane-1-carboxylic acid, the present inventors have achieved the invention based on finding that an esterase derived from a microorganism belonging to Genus Arthrobacter can act on 2,2-dimethyl-3-(substituted vinyl)cyclopropane-1-carboxylic acid esters represented by the general formula (2): ##STR3##
(wherein X is a hydrogen atom or a chlorine atom; Y is a methyl group when X is a hydrogen atom, whereas Y is a methyl group or a fluorine atom when X is a chlorine atom; and R is a C.sub.1 -C.sub.4 alkyl group) so that the ester is asymmetrically hydrolyzed.